Mandeep K.

asked • 12/22/19

I need help with a mix of microbiology/biochem/pharma/stereochem, see details below.

Hello, I need help with a mix of microbiology/biochem/pharma. I did an experiment where I made mimics of TB antibiotics in a lab. I need to understand the structural activity relationship of the compound or stereochemistry. I tested this on a bacteria as a kirby bauer disk test. The variations I made didnt inhibit the bacteria. I need to know why not and whats the mechanism of action [MOA] of my compound/drug molecule. I have an idea regarding the MOA, I just need verification. 

Brian L.

Are you dealing with different classes of antibiotics or are you seeking to determine the structural activity relationship based on the results of your experiment? In short, the bacteria in your experiment might not have been inhibited because the compound you tested did not have enough inhibitory activity at the site of action (which could be a bacterial enzyme, cellular protein, etc.). Slight modifications of the drug's structure can have a dramatic effect on its efficacy. Likewise, two drugs with the same molecular formula but different stereochemistry (such as enantiomers) can have different activities. There are many real-life examples of this. Please share any other information you have about this experiment, so I could be of further assistance.
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12/23/19

Mandeep K.

Not different classes of antibiotics just seeking to determine the structural activity relationship. Absolutely, due to modifications there will be an effect on bacterial activity. For sure, it wasnt inhibited. I need to know what can be the mechanism of action for my parent compound. I also need to understand what are the exact changes made mean. Please and thank you.
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12/23/19

Robert S.

Which TB antibiotic did you model after? Rifampin? Isoniazid?
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01/04/20

1 Expert Answer

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Matt S. answered • 01/20/20

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Have you run any NMR or Mass Spec? Running a simple 1H NMR (proton nuclear magnetic resonance) and GC or LC-MS (gas chromatography or liquid chromatography mass spectrum) will help you know more about the structure. Did you synthesize it in lab (like organic synthesis)? If so you should definitely have the tools to find the structure. I'm pretty sure GC-MS can separate enantiomers (stereochem) and 1H NMR should have a different shift for R vs S.


Let me know if this helps!

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